ES2340178T3 - Compuestos biaromaticos que son activadores de los receptores astivados tipo ppar (gamma), su proceso de preparacion y su utilizacion en composiciones cosmeticas o farmaceuticas. - Google Patents

Compuestos biaromaticos que son activadores de los receptores astivados tipo ppar (gamma), su proceso de preparacion y su utilizacion en composiciones cosmeticas o farmaceuticas. Download PDF

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Publication number: ES2340178T3
Authority: ES; Spain
Prior art keywords: radical; compound; group; acid; alkyl
Prior art date: 2004-05-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES05743226T

Other languages

English (en)

Spanish (es)

Inventor

Jerome Aubert

Laurence Clary

Pascale Mauvais

Michel Rivier

Etienne Thoreau

Jean-Guy Boiteau

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Galderma Research and Development SNC

Original Assignee

Galderma Research and Development SNC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2004-05-06

Filing date

2005-04-29

Publication date

2010-05-31

2005-04-29 Application filed by Galderma Research and Development SNC filed Critical Galderma Research and Development SNC

2010-05-31 Application granted granted Critical

2010-05-31 Publication of ES2340178T3 publication Critical patent/ES2340178T3/es

2025-04-29 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 121
238000002360 preparation method Methods 0.000 title claims description 40
239000002537 cosmetic Substances 0.000 title claims description 11
239000008194 pharmaceutical composition Substances 0.000 title claims description 6
102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title description 31
108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title description 31
239000012190 activator Substances 0.000 title description 7
-1 hexenyl radical Chemical class 0.000 claims abstract description 118
239000000203 mixture Substances 0.000 claims abstract description 70
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 47
150000003254 radicals Chemical class 0.000 claims abstract description 36
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 14
125000003118 aryl group Chemical group 0.000 claims abstract description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 12
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 12
125000000524 functional group Chemical group 0.000 claims abstract description 12
125000005843 halogen group Chemical group 0.000 claims abstract description 12
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 12
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims abstract description 12
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 12
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims abstract description 11
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims abstract description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 11
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 11
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims abstract description 9
230000003287 optical effect Effects 0.000 claims abstract description 9
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims abstract description 9
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims abstract description 9
239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
125000006038 hexenyl group Chemical group 0.000 claims abstract description 8
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 8
VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical group CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 claims abstract description 8
229920000570 polyether Polymers 0.000 claims abstract description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
150000005840 aryl radicals Chemical class 0.000 claims abstract description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 7
235000010290 biphenyl Nutrition 0.000 claims abstract description 6
239000004305 biphenyl Substances 0.000 claims abstract description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 5
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims abstract description 5
125000005907 alkyl ester group Chemical group 0.000 claims abstract description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims abstract description 4
125000005469 ethylenyl group Chemical group 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 73
238000006243 chemical reaction Methods 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
125000004429 atom Chemical group 0.000 claims description 18
208000035475 disorder Diseases 0.000 claims description 18
208000002874 Acne Vulgaris Diseases 0.000 claims description 13
206010000496 acne Diseases 0.000 claims description 13
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 12
229910052763 palladium Inorganic materials 0.000 claims description 11
150000002632 lipids Chemical class 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
230000002265 prevention Effects 0.000 claims description 9
FIVBDLFVVYKKKE-QFIPXVFZSA-N (2s)-2-ethoxy-3-[4-[3-[methyl(pentylcarbamoyl)amino]phenyl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 FIVBDLFVVYKKKE-QFIPXVFZSA-N 0.000 claims description 8
210000004027 cell Anatomy 0.000 claims description 8
229940126214 compound 3 Drugs 0.000 claims description 8
229940125898 compound 5 Drugs 0.000 claims description 8
230000035755 proliferation Effects 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
SJYMPJFKLQPLFB-DEOSSOPVSA-N (2s)-2-ethoxy-3-[4-[3-[heptylcarbamoyl(methyl)amino]phenyl]phenyl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 SJYMPJFKLQPLFB-DEOSSOPVSA-N 0.000 claims description 7
239000012948 isocyanate Substances 0.000 claims description 7
230000005855 radiation Effects 0.000 claims description 7
230000015572 biosynthetic process Effects 0.000 claims description 6
229940125782 compound 2 Drugs 0.000 claims description 6
230000004069 differentiation Effects 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
230000003780 keratinization Effects 0.000 claims description 6
230000004060 metabolic process Effects 0.000 claims description 6
229910001923 silver oxide Inorganic materials 0.000 claims description 6
208000017520 skin disease Diseases 0.000 claims description 6
238000003786 synthesis reaction Methods 0.000 claims description 6
125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
201000004384 Alopecia Diseases 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
208000012641 Pigmentation disease Diseases 0.000 claims description 5
XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims description 5
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 5
231100000360 alopecia Toxicity 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
230000008439 repair process Effects 0.000 claims description 5
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 4
BLLPPNGQNIZBCW-SANMLTNESA-N (2s)-2-(cyclopropylmethoxy)-3-[4-[3-[heptylcarbamoyl(methyl)amino]phenyl]phenyl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC3CC3)C(O)=O)=CC=2)=C1 BLLPPNGQNIZBCW-SANMLTNESA-N 0.000 claims description 4
ANBKFTDCKJTYII-VWLOTQADSA-N (2s)-3-[4-[3-[heptylcarbamoyl(methyl)amino]phenyl]phenyl]-2-propoxypropanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCCC)C(O)=O)=CC=2)=C1 ANBKFTDCKJTYII-VWLOTQADSA-N 0.000 claims description 4
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 4
DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 claims description 4
LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 claims description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
230000032683 aging Effects 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
229940125773 compound 10 Drugs 0.000 claims description 4
229940125797 compound 12 Drugs 0.000 claims description 4
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
238000005859 coupling reaction Methods 0.000 claims description 4
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims description 4
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 4
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
238000007127 saponification reaction Methods 0.000 claims description 4
201000010153 skin papilloma Diseases 0.000 claims description 4
239000012312 sodium hydride Substances 0.000 claims description 4
229910000104 sodium hydride Inorganic materials 0.000 claims description 4
206010003645 Atopy Diseases 0.000 claims description 3
239000004593 Epoxy Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
206010020649 Hyperkeratosis Diseases 0.000 claims description 3
208000001126 Keratosis Diseases 0.000 claims description 3
230000033228 biological regulation Effects 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229940125904 compound 1 Drugs 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
230000002500 effect on skin Effects 0.000 claims description 3
208000026278 immune system disease Diseases 0.000 claims description 3
230000004968 inflammatory condition Effects 0.000 claims description 3
230000002757 inflammatory effect Effects 0.000 claims description 3
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 3
230000003211 malignant effect Effects 0.000 claims description 3
230000011987 methylation Effects 0.000 claims description 3
238000007069 methylation reaction Methods 0.000 claims description 3
230000019612 pigmentation Effects 0.000 claims description 3
230000003612 virological effect Effects 0.000 claims description 3
SJYMPJFKLQPLFB-XMMPIXPASA-N (2r)-2-ethoxy-3-[4-[3-[heptylcarbamoyl(methyl)amino]phenyl]phenyl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@@H](OCC)C(O)=O)=CC=2)=C1 SJYMPJFKLQPLFB-XMMPIXPASA-N 0.000 claims description 2
FIVBDLFVVYKKKE-JOCHJYFZSA-N (2r)-2-ethoxy-3-[4-[3-[methyl(pentylcarbamoyl)amino]phenyl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@@H](OCC)C(O)=O)=CC=2)=C1 FIVBDLFVVYKKKE-JOCHJYFZSA-N 0.000 claims description 2
AYVKOBFMOFGFSV-QHCPKHFHSA-N (2s)-2-(cyclopropylmethoxy)-3-[4-[3-[cyclopropylmethylcarbamoyl(methyl)amino]phenyl]phenyl]propanoic acid Chemical compound C=1C=CC(C=2C=CC(C[C@H](OCC3CC3)C(O)=O)=CC=2)=CC=1N(C)C(=O)NCC1CC1 AYVKOBFMOFGFSV-QHCPKHFHSA-N 0.000 claims description 2
REUCFCZZMFQLSR-DEOSSOPVSA-N (2s)-2-(cyclopropylmethoxy)-3-[4-[3-[methyl(pentylcarbamoyl)amino]phenyl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC3CC3)C(O)=O)=CC=2)=C1 REUCFCZZMFQLSR-DEOSSOPVSA-N 0.000 claims description 2
RNLFKMZQTNZFJA-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[3-[methyl(propylcarbamoyl)amino]phenyl]phenyl]propanoic acid Chemical compound CCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 RNLFKMZQTNZFJA-FQEVSTJZSA-N 0.000 claims description 2
XBHQOMRKOUANQQ-BYPYZUCNSA-N (2s)-2-ethoxypropanoic acid Chemical compound CCO[C@@H](C)C(O)=O XBHQOMRKOUANQQ-BYPYZUCNSA-N 0.000 claims description 2
SWCFAEPNTNAODB-NRFANRHFSA-N (2s)-2-methoxy-3-[4-[3-[methyl(pentylcarbamoyl)amino]phenyl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OC)C(O)=O)=CC=2)=C1 SWCFAEPNTNAODB-NRFANRHFSA-N 0.000 claims description 2
KALHNSQTKNUZPV-VWLOTQADSA-N (2s)-3-[4-[3-[2-cyclohexylethylcarbamoyl(methyl)amino]phenyl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCCC2CCCCC2)=C1 KALHNSQTKNUZPV-VWLOTQADSA-N 0.000 claims description 2
ZOBDJYQSRAPXIX-QHCPKHFHSA-N (2s)-3-[4-[3-[cyclopentylmethylcarbamoyl(methyl)amino]phenyl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCC2CCCC2)=C1 ZOBDJYQSRAPXIX-QHCPKHFHSA-N 0.000 claims description 2
XOEAUMDENHQWAC-NRFANRHFSA-N (2s)-3-[4-[3-[cyclopropylmethylcarbamoyl(methyl)amino]phenyl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCC2CC2)=C1 XOEAUMDENHQWAC-NRFANRHFSA-N 0.000 claims description 2
SOPKJGCQANNHPS-QHCPKHFHSA-N (2s)-3-[4-[3-[heptylcarbamoyl(methyl)amino]phenyl]phenyl]-2-methoxypropanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OC)C(O)=O)=CC=2)=C1 SOPKJGCQANNHPS-QHCPKHFHSA-N 0.000 claims description 2
FEICJPCZQDNGKQ-QHCPKHFHSA-N (2s)-3-[4-[3-[methyl(pentylcarbamoyl)amino]phenyl]phenyl]-2-propoxypropanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCCC)C(O)=O)=CC=2)=C1 FEICJPCZQDNGKQ-QHCPKHFHSA-N 0.000 claims description 2
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Classifications

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- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P17/08—Antiseborrheics
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- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
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Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Dermatology (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Hematology (AREA)
Obesity (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Immunology (AREA)
Neurosurgery (AREA)
Vascular Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Urology & Nephrology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Child & Adolescent Psychology (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)

ES05743226T 2004-05-06 2005-04-29 Compuestos biaromaticos que son activadores de los receptores astivados tipo ppar (gamma), su proceso de preparacion y su utilizacion en composiciones cosmeticas o farmaceuticas. Expired - Lifetime ES2340178T3 (es)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR0404913		2004-05-06
FR0404913A FR2869903B1 (fr)	2004-05-06	2004-05-06	Nouveaux composes bi-aromatiques activateurs des recepteurs de type ppary, leur procede de preparation et leur utilisation dans les compositions cosmetiques ou pharmaceutiques
US57421704P	2004-05-26	2004-05-26
US574217P		2004-05-26

Publications (1)

Publication Number	Publication Date
ES2340178T3 true ES2340178T3 (es)	2010-05-31

Family

ID=34945757

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES05743226T Expired - Lifetime ES2340178T3 (es)	2004-05-06	2005-04-29	Compuestos biaromaticos que son activadores de los receptores astivados tipo ppar (gamma), su proceso de preparacion y su utilizacion en composiciones cosmeticas o farmaceuticas.

Country Status (18)

Country	Link
EP (1)	EP1742608B1 (pl)
JP (1)	JP2007536331A (pl)
KR (1)	KR20070015566A (pl)
CN (1)	CN1950335A (pl)
AR (1)	AR048884A1 (pl)
AT (1)	ATE458468T1 (pl)
AU (1)	AU2005240345A1 (pl)
BR (1)	BRPI0510223A (pl)
CA (1)	CA2563955A1 (pl)
DK (1)	DK1742608T3 (pl)
ES (1)	ES2340178T3 (pl)
FR (1)	FR2869903B1 (pl)
PL (1)	PL1742608T3 (pl)
PT (1)	PT1742608E (pl)
RU (1)	RU2006143054A (pl)
SI (1)	SI1742608T1 (pl)
WO (1)	WO2005108352A1 (pl)
ZA (1)	ZA200609806B (pl)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US11241420B2 (en)	2007-04-11	2022-02-08	Omeros Corporation	Compositions and methods for prophylaxis and treatment of addictions
US20160331729A9 (en)	2007-04-11	2016-11-17	Omeros Corporation	Compositions and methods for prophylaxis and treatment of addictions
CN105164104B (zh) *	2013-03-20	2019-04-12	豪夫迈·罗氏有限公司	脲衍生物及其作为脂肪酸结合蛋白(fabp)抑制剂的用途
KR101804650B1 (ko) *	2013-03-20	2018-01-10	에프. 호프만-라 로슈 아게	우레아 유도체 및 이의 지방산 결합 단백질(fabp) 억제제로서의 용도
CN104844476B (zh) *	2015-04-03	2016-08-24	李凌	一种医药中间体联苯类化合物的合成方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2812876B1 (fr) *	2000-08-08	2002-09-27	Galderma Res & Dev	Nouveaux composes bi-aromatiques activateurs des recepteurs de type ppar-gamma et leur utilisation dans des compositions cosmetiques ou pharmaceutiques
PL376736A1 (pl) *	2002-11-25	2006-01-09	Galderma Research & Development, S.N.C.	Nowe związki diaromatyczne, które aktywują receptor typu PPAR<$Egamma> i ich zastosowanie w kompozycjach kosmetycznych lub farmaceutycznych

2004
- 2004-05-06 FR FR0404913A patent/FR2869903B1/fr not_active Expired - Fee Related
2005
- 2005-04-29 AU AU2005240345A patent/AU2005240345A1/en not_active Abandoned
- 2005-04-29 AT AT05743226T patent/ATE458468T1/de active
- 2005-04-29 JP JP2007512127A patent/JP2007536331A/ja active Pending
- 2005-04-29 PT PT05743226T patent/PT1742608E/pt unknown
- 2005-04-29 RU RU2006143054/04A patent/RU2006143054A/ru unknown
- 2005-04-29 EP EP05743226A patent/EP1742608B1/en not_active Expired - Lifetime
- 2005-04-29 CA CA002563955A patent/CA2563955A1/en not_active Abandoned
- 2005-04-29 WO PCT/EP2005/005797 patent/WO2005108352A1/en not_active Ceased
- 2005-04-29 CN CNA2005800145211A patent/CN1950335A/zh active Pending
- 2005-04-29 KR KR1020067023286A patent/KR20070015566A/ko not_active Withdrawn
- 2005-04-29 PL PL05743226T patent/PL1742608T3/pl unknown
- 2005-04-29 SI SI200530933T patent/SI1742608T1/sl unknown
- 2005-04-29 DK DK05743226.2T patent/DK1742608T3/da active
- 2005-04-29 ES ES05743226T patent/ES2340178T3/es not_active Expired - Lifetime
- 2005-04-29 BR BRPI0510223-5A patent/BRPI0510223A/pt not_active Application Discontinuation
- 2005-05-04 AR ARP050101786A patent/AR048884A1/es unknown
2006
- 2006-11-23 ZA ZA200609806A patent/ZA200609806B/en unknown

Also Published As

Publication number	Publication date
CN1950335A (zh)	2007-04-18
CA2563955A1 (en)	2005-11-17
BRPI0510223A (pt)	2007-10-23
RU2006143054A (ru)	2008-06-20
EP1742608B1 (en)	2010-02-24
PL1742608T3 (pl)	2010-07-30
PT1742608E (pt)	2010-04-27
AR048884A1 (es)	2006-06-07
EP1742608A1 (en)	2007-01-17
FR2869903B1 (fr)	2006-06-23
ATE458468T1 (de)	2010-03-15
SI1742608T1 (sl)	2010-04-30
DK1742608T3 (da)	2010-05-17
WO2005108352A1 (en)	2005-11-17
AU2005240345A1 (en)	2005-11-17
FR2869903A1 (fr)	2005-11-11
KR20070015566A (ko)	2007-02-05
JP2007536331A (ja)	2007-12-13
ZA200609806B (en)	2007-12-27

Publication	Publication Date	Title
AU2001285981B2 (en)	2006-01-19	Biphenyl derivatives and their use as PPAR-GAMMA receptor activators
US20090062340A1 (en)	2009-03-05	Novel biaromatic compounds which activate ppary type receptors and cosmetic/pharmaceutical compositions comprised thereof
EP1781274B1 (en)	2008-11-05	Novel biaromatic compounds which activate receptors of ppar type and their use in cosmetic or pharmaceutical compositions
US20070207175A1 (en)	2007-09-06	Biaromatic compound activators of PPARgamma receptors and cosmetic/pharmaceutical compositions comprised thereof
FR2892412A1 (fr)	2007-04-27	Composes biaromatiques modulateurs des ppars
US7973063B2 (en)	2011-07-05	Methods for activating PPAR gamma-type receptors
JP2006509798A (ja)	2006-03-23	ＰＰＡＲγ型受容体を調節する新規化合物、および化粧品組成物または医薬組成物におけるその使用
EP1742608B1 (en)	2010-02-24	Biaromatic compounds which activate ppar(gamma) type receptors, their process of preparation and their use in cosmetic or pharmaceutical compositions
ES2357183T3 (es)	2011-04-19	Nuevos derivados de ácido 3-fenil propanoico activadores de los receptores de tipo ppar, su método de preparaciòn y su utilización en composiciones cosméticas o farmacéuticas.
JP2008509966A (ja)	2008-04-03	Ｐｐａｒタイプ受容体を活性化する新規な二芳香族化合物および化粧品組成物または医薬組成物でのその使用
MXPA05005334A (es)	2005-11-17	Compuestos bifenilo activadores de los receptores de tipo receptores activados de la proliferacion de peroxisoma gamma y su uso en composiciones cosmeticas o farmaceuticas.
FR2878247A1 (fr)	2006-05-26	Nouveaux composes modulateurs des recepteurs de type ppary et leur utilisation dans des compositions cosmetiques ou pharmaceutiques
FR2848553A1 (fr)	2004-06-18	Nouveaux composes modulateurs des recepteurs de type ppary et leur utilisation dans des compositions cosmetiques ou pharmaceutiques
EP1963249A1 (fr)	2008-09-03	Derives biphenyliques agonistes selectifs du recepteur rar-gamma
ES2285554T3 (es)	2007-11-16	Nuevos compuestos que son moduladores de receptores de tipo ppar y su uso en composiciones cosmeticas o farmaceuticas.
EP1828124A1 (en)	2007-09-05	Biaromatic compounds that modulate ppar type receptors, process for preparing them and use thereof in cosmetic or pharmaceutical compositions
MX2007006014A (es)	2007-11-14	Compuestos que modulan receptores tipo ppar-gamma y uso de los mismos en composiciones cosmeticas y farmaceuticas.
ES2360584T3 (es)	2011-06-07	Compuestos que modulan receptores de tipo ppar y el uso de los mismos en composiciones cosméticas o farmacéuticas.